Sodium Chloride → 3-(4-Hydroxyphenyl)hex-4-ynoic acid

HRID 2375724Notes

Reaction equation

HRID 2375724 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]2C(=O)OC(C)(C)[O:14][C:13]2=[O:21])[C:9]#[C:10][CH3:11])=[CH:4][CH:3]=1.C(C(CC)=O)C.[Na+].[Cl-]>O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]#[C:10][CH3:11])[CH2:12][C:13]([OH:21])=[O:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 7288Ethyl ketoneHCID 598551335-(1-(4-Hydroxyphenyl)but-2-yn-1-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 598551363-(4-Hydroxyphenyl)hex-4-ynoic acidYield 77.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1 L round bottom flask was charged with compound 1.2 (37 g), diethyl ketone (160 mL), and water (80 mL). The suspension was heated to reflux for 48 hours. After cooling, the aqueous layer was saturated with NaCl(s) and separated. The organic layer was dried over MgSO4, filtered, and concentrated to a light brown oil which was crystallized from hot EtOAc:hexanes (1:2). After collecting and drying, the product was obtained as an off-white powder (20.3 g). 1H NMR (500 MHz, DMSO-d6) δ 12.2 (s, 1H); 9.27 (s, 1H); 7.12 (d, 2H, J=8.5 Hz); 6.67 (d, 2H, J=8.6 Hz); 3.87 (m, 1H); 2.54 (m, 2H); 1.82 (d, 3H, J=2.4 Hz). MS ESI (pos.) m/e: 205.1 (M+H); 227.1 (M+Na).

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 48 hours
  3. temperatureAfter cooling
  4. customseparated
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a light brown oil which
  8. customwas crystallized from hot EtOAc:hexanes (1:2)
  9. customAfter collecting
  10. customdrying

Sources & evidence

ORD record
ord-3f37ab3d10154e06ae88d7c1b2c32639
Source dataset
uspto-grants-2008_12
Patent number
US07465804B2

Reaction notes

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